“People say, ‘You may have been the difference in the election,’ ” says Olbermann. He gives a shudder. I can’t tell whether it’s genuine revulsion or managed humility. “I’m like, ‘Oh, Christ, I don’t want that.’ I’m not out for some power trip on this. I have some personal and professional ambition, but in terms of influence, I just want to see the truth out there.”
Olbermann says he doesn’t vote, and he insists his Bush bashing isn’t ideological. “Look, I didn’t begin this show in 2003 with ‘This is a damn-fool war,’ ” says Olbermann. “We in the media were guilty of assuming our government wouldn’t lie to get us into war. We were largely exploited because we gave them the benefit of the doubt after 9/11. They couldn’t have choreographed it any better if they tried. What angers me is their certainty. The closer you get to something, the less certain you should be of your position. That doesn’t happen with these people. The number of opportunities and chances to redirect this that have been missed is tragic.”
Up until January, everyone who counted was a Republican, says Olbermann. “If the Democrats continue to drag their feet on what the country surely wants, which is non-escalation, I’ll go after them in the same terms: ‘Why are you not listening? Who do you think you answer to?’ ”
It may be true that the roots of Olbermann’s rage aren’t political, strictly speaking. His anti-Bush rants are as much about a kind of reflexive populist anger as anything. But it’s also true that Olbermann doesn’t tend to go after Democrats with the same bloodthirsty zeal with which he attacks the Republicans. In January, when Olbermann asked Hillary Clinton, “Would you apply the word mistake to your vote to authorize the war in Iraq?” she bobbed and weaved and never answered the question. Olbermann didn’t follow up and instead steered the dialogue to safer ground. In October, Olbermann ran a prerecorded segment of an interview he did with Bill Clinton, at the end of the Clinton Global Initiative meetings. One of the ideas discussed at the conference involved creating educational opportunities in Africa. Before he asked his first question, Olbermann handed Bill a check, saying, “Here’s eight more schools in Kenya from me.” While the thought might have been noble, the gesture didn’t exactly smack of political objectivity.
It probably won’t come as much of a surprise that when Keith Olbermann was a kid, he got the tar kicked out of him on a regular basis. And not by the football team. “I got beat up by girls all the time,” says Olbermann. “They literally posted a sign-up sheet and would take turns. I think that’s why I’ve always been such a fan of Mencken’s line, ‘Afflict the comfortable and comfort the afflicted.’ I’ve been afflicted.”
Olbermann’s affliction began at age 5, when his Westchester parents—his father was an architect, his mother a preschool teacher—jumped Olbermann from kindergarten to second grade. “I don’t recommend that,” says Olbermann. “I was always trying to match my intellectual maturity with an equal emotional maturity, and it didn’t work.”
At age 9, Olbermann started collecting baseball cards, even climbing into Dumpsters to collect special 3-D editions thrown out with Twinkie boxes. On television, Olbermann was entranced by former iconoclastic Yankee turned New York sports anchor Jim Bouton. On the radio, he avidly listened to Bob and Ray, the deadpan New York comedy duo who dominated the AM dial in the fifties and sixties. He also memorized late-night reruns of Murrow broadcasts. In junior high, Olbermann spent his summers poring over transcripts of the Army-McCarthy hearings and reading Teddy White’s Making of the President books.
By high school, Olbermann decided he wanted to be a broadcaster. At the Hackley School in Tarrytown, he met an older kid named Chris Berman (the future ESPN fixture), and the two classmates ran a half-watt school radio station. Graduating at 16, Olbermann shipped off to Cornell as the school’s youngest freshman. It wasn’t much fun. His parents went to extreme lengths to make his dorm room the only one in Ithaca with cable TV. Between tearful calls home, Olbermann sat alone and watched the tube. “Thank God for Monty Python’s Flying Circus,” says Olbermann. “Or I might not have made it.”
Olbermann skipped classes to report for his college radio station on the championship Yankees teams of the late seventies. After graduating, he landed sports-anchor jobs in Boston and Los Angeles. Olbermann’s L.A. sportscast sometimes finished seventh behind reruns of Spanish-language soap operas, but people noticed the quirky guy who once ate prime rib during a broadcast.
In 1992, ESPN director of programming John Walsh hired Olbermann and paired him with Dan Patrick to host the 11 p.m. edition of SportsCenter. The smart-ass New Yorker and the Ohio high-school hoops star quickly established a winning, irreverent rapport. There were T-shirt-launching catchphrases, like Patrick’s “En fuego” and Olbermann’s “If you’re scoring at home, or even if you’re alone ... ,” and the pair became the model for sports anchors as TV stars. Eventually, Aaron Sorkin would base his sitcom SportsNight on the duo. (Olbermann once claimed that both characters were based on him.)